These groups are generally better connected among themselves than with other groups, so you are probably better advised to target them on this basis. As it’s your first time to Greece, you may want the full-on Greek island experience and you could easily fill your five weeks flitting from one island to the other in the Cyclades. You could start in Kea and work your way down to Milos via Kythnos, Serifos and Sifnos then segue to Paros and Naxos. Dip down to Santorini, up to Mykonos and back to Piraeus. The map will also show plenty of other Cyclades islands to pick and choose from such as Ios, Sikinos, Folegandros, Amorgos, Syros, Tinos and Andros – yes! too many choices, but you will find that sticking to one group it will be easier to get between them. Realistically for a period of five weeks you will not want to be doing more than 6-8 islands.
Though this country has some 322 islands, less than a third are inhabited. Most of the action happens in the western islands, but no matter where you go, this is heaven. Any time the name Fiji is heard, visions of beaches and tropical ocean dance in people’s head. There’s a good reason for that – because this place is one of the best places to go in the world, and with so many islands, you’re bound to find one you like. 

I think Naxos would be the best island for you: incredible beaches, wonderful villages, great restaurants, and some very good hotels (though I don’t think I’d go so far as to call them hip – but nice, for sure). The farther south you go from Naxos Town the quieter the beaches get – so keep going to find the balance you prefer. If you want an island with a little more hip but beaches not quite as perfect then try Paros. If you want to err on the quieter and idyllic side then Antiparos or Ikaria.
They are located north of Australia and east of Bali and offer stunning tropical scenery, a remarkable history, friendly villages, and some of the globe’s most pristine, biologically diverse coral reefs. The only way to reach them is to island-hop the Indonesian archipelago by small planes, ferry services, or eco-friendly cruises for serious divers but it is more than worth the trouble.
I’m a little worried I’ll get bored in Milos. My husband likes to stay in one place, but I like exploring. We would have split our time more evenly but we want to stay on the caldera and it’s just too expensive to stay any longer than two or three nights. Alternatively, we could stay in Santorini for longer but move to a cheaper hotel. Perhaps Santorini 6 nights and Milos 6 nights?

Yes, I would agree that 8 or 9 days is too long for Naxos – unless you’re happy sitting at the beach for several of those days. But if you’re looking to be semi-active and explore then you’d be best to add Paros and spend 4/5 days on each. Crete, on the other hand, would be perfect for an 8/9 day road trip. Start in Heraklion (where the ferry arrives from Santorini) head east and then south and finally ending up in the western town of Chania where you can fly up home from.

You’d have to check the schedule for your specific dates but I think Santorini then Milos then Paros then Naxos and Athens would probably be the best order. 3 days in each sounds great. Or a small tweak: 2 days in Milos and then 4 days in Santorini (splitting time between 2 of the 4 caldera towns) or even 4 days in Paros (splitting time between Naousa and Parikia).
Remote and unspoiled Crooked Island has little in the way of tourist facilities, but it does boast gorgeous beaches, bat caves and flamingos, and also serves as a turtle nesting spot. One of the four islands that form an atoll hugging the striking shallow waters of the Bight of Acklins, it hasn’t much changed since Columbus sailed down the leeward side through the narrow Crooked Island Passage. There are miles of untouched, white powdery sands, coral gardens, limestone caves and cliffs, remnants of slave and cotton plantations, ancient churches, fortifications and mangrove-lined waterways.
×